Keep Getting "Outlook closed while you had items open. Reopen items from last session?" Even Though It's Not True

Unchecking that "Store My Outlook Settings In the Cloud" was one of the very first things I did when I got my (then)new pc back over a year ago and set up Office, and I have verified that that box is still unchecked, and I still get 'occasional' "Reopen Items..." messages when I start Outlook.

Ever since someone tried to file a tax return in my name about 5 years ago, and then 2 years ago tried filing for state unemployment in my wife's name I don't trust ANY piece of personal information to 'The Cloud'. Heck, even just the act of transmitting that kind of data across the ether from my secure storage to their secure storage is open for possible hacking. So, when I found that "Help" won't work in MS Word UNLESS you allow MS to transmit usage data to their servers 'to allow them to make the application better', I was not happy in the least. But, what ya gonna do...?

I did not select my post with the added registry key as the Answer to this problem (someone else did). That registry key is Microsoft's work around until they release a fix for this problem., which doesn't work for some users.

There are several answers that work for some and don't work for others, but the Answers that work for all are:

1. Reverting to the version of Outlook (2305) before the bad update caused this problem.
2. As Paul from London pointed out by Not keeping your Outlook settings in the cloud (term for on the Mail server). I don't believe the registry key is needed as this is a cloud problem with Outlook. Why? see # 3 below.
3. Delete all emails from the mail server before closing Outlook. I download and keep the emails I want by transferring the emails to a separate Outlook Data file that is keep on my HDD. I delete all other emails and copies of emails I kept from the server so there are no emails left on the server when I close Outlook. I never had even one occurrence of this popup query from Outlook, yet I did get the update that causes problems for other users.

#2 and # 3 above clearly point to the mail server's emails being the "items to be reopened". I believe the message occurs because Outlook is closed before all the mail folders in Outlook have not synchronized with the same folders on the mails server (cloud) and that discrepancy upon opening causes the message to occur.

To test this, I would like someone that gets these messages often to try synchronizing all the folders before closing Outlook and see if that stops the popup query.

To synchronize a folder, just select the folder in the Navigation pane; which will display "Synchronizing Folder Name" at the bottom of Outlook as shown in the image below. Synchronize each folder before closing Outlook.

Unchecking that "Store My Outlook Settings In the Cloud" was one of the very first things I did when I got my (then)new pc back over a year ago and set up Office, and I have verified that that box is still unchecked, and I still get 'occasional' "Reopen Items..." messages when I start Outlook.

Ever since someone tried to file a tax return in my name about 5 years ago, and then 2 years ago tried filing for state unemployment in my wife's name I don't trust ANY piece of personal information to 'The Cloud'. Heck, even just the act of transmitting that kind of data across the ether from my secure storage to their secure storage is open for possible hacking. So, when I found that "Help" won't work in MS Word UNLESS you allow MS to transmit usage data to their servers 'to allow them to make the application better', I was not happy in the least. But, what ya gonna do...?

Well as far as I am aware, the cloud setting in this case saves your outlook settings there.

This is to my knowledge to allow better roaming between machines where your settings will roam to all machines you login onto.

When disabling the save settings onto the cloud you will have to add that Registry value due to its now no longer saving onto the cloud and needs to know what to do.

It has nothing to do with emails left on the mail server, I have emails on my mail server and don't get the issue.

The issue is the Cloud saving the settings, when using Cloud Save the ReopenWindowsOption registry value is not needed, BUT if saving the settings to the cloud is disabled, that registry key is needed and needs to be set to a value of 1 this is to say what to do when starting Outlook.

Once again, the Cloud feature in Outlook just saves the settings for Outlook and nothing more, it says that in that section of the settings, its to allow roaming between Computers.